Ethylmorphine

Death may occur when opiates are combined with depressants such as benzodiazepines, alcohol or other GABAergic substances. Taking large amounts of these substances together is strongly discouraged.

Ethylmorphine
The skeletal formula of ethylmorphine
Chemical Nomenclature
Common names	Ethylmorphine, codethyline, dionine
Substitutive name	3-ethylmorphine
Systematic name	7,8-didehydro-4,5-α-epoxy- 3-ethoxy-17-methylmorphinan-6-α-ol
Class Membership
Psychoactive class	Depressant
Chemical class	Opioid
Routes of Administration
Oral Dosage WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section. DISCLAIMER: PW's dosage information is a summary of data gathered from users and resources. It is NOT a recommendation and should be verified with other sources for accuracy. Threshold < 20 mg Light 50 - 75 mg Common 75 - 200 mg Strong 250 mg Duration Total 2 - 4 hours

Summary sheet: Ethylmorphine

Ethylmorphine, also known as codethyline and dionine, is a semi-synthetic opioid first created by Merck in 1884 and used as a weaker alternative to morphine. Today, it is most commonly used as an antitussive which is available in cough syrup preparations like Cocillana, Cosylan, Solvipect comp. (in combination with guaifenesin) and Lepheton (in combination with ephedrine), or in tablet form sold as Tussipax (in combination with codeine). Cough syrup preparations commonly include a mild laxative to counter the constipation which is a common side effect of opioids. Ethylmorphine is also used in ophthalmic preparations as dionine to treat inflammations of the eye. In 1904, an ethylmorphine preparation was described as "a new ocular analgesic."

Chemistry

Ethylmorphine, or 3-ethylmorphine, is an opioid of the morphinan class. Ethylmorphine and other molecules of this class contain a polycyclic core of three benzene rings fused in a zig-zag pattern called phenanthrene. A fourth nitrogen containing ring is fused to the phenanthrene at R₉ and R₁₃ with the nitrogen member looking at R₁₇ of the combined structure. This structure is called morphinan.

Ethylmorphine, along with other morphinans, contains an ether bridge between two of its rings, connecting R₄ and R₅ through an oxygen group. It contains a hydroxy group (OH-) bound at R₆ and a methyl group located on the nitrogen atom at R₁₇. On the same ring containing the hydroxy group, ethylmorphine contains a double bond which is shared with codeine and morphine.

Ethylmorphine is closely related to morphine; both contain an oxygen group at R₃, but this oxygen group in ethylphenidate is substituted by a ethyl group (making an ethoxy group). Ethylmorphine differs from the naturally occurring codeine (3-methylmorphine) only in having an ethoxy group in place of the methoxy group (they are homologous). It is also analogous to the other morphinans such as dihydrocodeine, heroin, hydrocodone, and oxycodone.

Pharmacology

Like codeine, ethylmorphine is a prodrug for morphine which exerts its effects primarily by binding to and activating the μ-opioid receptor. The metabolism of ethylmorphine is similar to that of codeine, so please refer to that article for more details. Ethylmorphine is metabolized into morphine by the cytochrome P450 enzyme CYP2D6. In addition to O-deethylation to morphine, ethylmorphine can also be N-demethylated to norethylmorphine and glucuronidated to ethylmorphine-6-glucuronid in humans.

Ethylmorphine has been described as less potent than morphine but slightly more potent than codeine.

Subjective effects

The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.

Physical effects

The cognitive effects of ethylmorphine can be broken down into several components which progressively intensify proportional to dosage. The general head space of codeine is described by many as one of intense euphoria, relaxation, anxiety suppression and pain relief.

The most prominent of these physical effects generally include:

• Pain relief - This component is subjectively different from other anaesthetics as it does not necessarily remove the pain entirely while still remaining equal in terms of its effectiveness. Instead of directly suppressing pain, these substances simply dull the perceived sensation and cover it up with feelings of physical and emotional pleasure.
• Euphoria - This particular substance can be considered as less intense in its physical euphoria when compared with that of morphine or diacetylmorphine (heroin) due to the upper limit of how much can be converted into its active form through metabolism.
• Itchiness
• Respiratory depression
• Constipation
• Cough suppression
• Difficulty urinating
• Nausea
• Stomach cramps
• Sedation
• Pupil constriction

Cognitive effects

The physical effects of ethylmorphine can be broken down into several components which progressively intensify proportional to dosage.

These are described below and generally include:

• Euphoria - Like codeine, this particular substance can be considered as less intense in its cognitive euphoria when compared with that of morphine or diacetylmorphine (heroin) due to the upper limit of how much can be converted into its active form through metabolism. It is still, however, capable of extreme intensity and overwhelming bliss at heavier dosages with a low tolerance. The sensation itself can be described as powerful and overwhelming feeling of emotional bliss, contentment, and happiness.
• Anxiety suppression
• Compulsive redosing

Toxicity and harm potential

Like its cousin codeine and other opioids, ethylmorphine appears to be physically benign in reasonable doses.

Lethal dosage

One source estimates the minimum lethal dose at 500 mg. Codeine and ethylmorphine are widely believed to be safer than other opioids due to the ceiling effect. This occurs when the enzymes that convert the inactive drug into the active metabolite morphine become saturated. However, lethal overdoses of ethylmorphine are attested.

Mouse and rat oral LD50 are 520mg/kg and 810mg/kg, respectively.

Tolerance and addiction potential

Tolerance to many of the effects of ethylmorphine develops with prolonged use, including therapeutic effects. The rate at which this occurs develops at different rates for different effects.

As with other opioid drugs, chronic use of ethylmorphine can be considered highly addictive and is capable of causing both physical and psychological dependence. When physical dependence has developed, withdrawal symptoms may occur if a person suddenly stops their usage.

Interactions

Although mixing opioids with other depressants is always dangerous due to the potentiation of effects (including respiratory depression) combinations with alcohol are doubly dangerous. Ethanol not only mixes synergistically with the depressant effect of morphine (the active metabolite of codeine and ethylmorphine), but it also reduces the elimination rate; in vitro experiments with rat hepatocytes (liver tissue) showed that peak concentrations of morphine with 100 mM ethanol were 1.4 and 1.3 times higher than in controls for ethylmorphine and codeine, respectively.

Legal issues

• Internationally: Ethylmorphine is listed in the Single Convention on Narcotic Drugs in Schedule III.
• France: Tussipax tablets containing 10 mg of ethylmorphine and 10 mg of codeine are sold over the counter.
• Norway: Cosylan and Solvipect comp. cough syrups containing ethylmorphine hydrochloride 1.7mg/mL and 2.5mg/mL, respectively, are regulated in prescription Class B. They are commonly prescribed for dry cough.
• Sweden: Cocillana-Etyfin cough syrup containing ethylmorphine 2.5mg/mL is sold as a prescription drug. The same goes for Lepheton, a combination containing 0.82 mg/mL ethylmorphine hydrochloride and 2.05 mg/mL ephedrine.
• United States: No preparations containing ethylmorphine are on the market in the US. Pure ethylmorphine is listed in Schedule II and combination products containing no more than ethylmorphine 3mg/mL (or 15 mg per dosage unit together with a non-narcotic active ingredient) are listed in Schedule III. Preparations containing no more than ethylmorphine 1mg/mL or 1mg/g are listed in schedule V. This is similar to codeine, but unlike codeine, ethylmorphine is not available for medical purposes in the United States.
• United Kingdom: Ethylmorphine is a Class B controlled substance under the Misuse of Drugs Act. This is the same class as codeine, but unlike codeine, there exist no legal preparations of ethylmorphine.

In general, ethylmorphine and codeine, owing to their structural and pharmacological similarity, are treated similarly by law in most countries.

See also

• Responsible use
• Ethylmorphine (Wikipedia)
• Codeine